Acetic Acid → HCID 86672491, compound

HRID 1896226Notes

Reaction equation

HRID 1896226 reaction equation
[CH3:1][NH:2][C:3]([C@@:5]12[CH2:10][C@@H:9]1[C@@H:8]([N:11]1[CH:19]=[N:18][C:17]3[C:12]1=[N:13][C:14]([Cl:48])=[N:15][C:16]=3[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][C:33]3[N:34]=[N:35][N:36]([C:38]4[CH:43]=[CH:42][C:41]([F:44])=[C:40]([N+:45]([O-])=O)[CH:39]=4)[CH:37]=3)[CH:23]=1)[C@H:7]([OH:49])[C@@H:6]2[OH:50])=[O:4].C(O)(=O)C>C(#N)C.[Zn]>[CH3:1][NH:2][C:3]([C@@:5]12[CH2:10][C@@H:9]1[C@@H:8]([N:11]1[CH:19]=[N:18][C:17]3[C:12]1=[N:13][C:14]([Cl:48])=[N:15][C:16]=3[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][C:33]3[N:34]=[N:35][N:36]([C:38]4[CH:43]=[CH:42][C:41]([F:44])=[C:40]([NH2:45])[CH:39]=4)[CH:37]=3)[CH:23]=1)[C@H:7]([OH:49])[C@@H:6]2[OH:50])=[O:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86672490HCID 86672490, compound

Product 1

HCID 86672491HCID 86672491, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent

Procedure

Zinc dust (3 mg, 0.045 mmol) was added to a solution of compound 203 (5 mg, 0.007 mmol) in acetonitrile (0.5 mL)-acetic acid (0.5 mL) at 0° C. After addition, the reaction mixture was brought to room temperature and stirred for 2 h under the same conditions. The reaction mixture was filtered on a Celite bed, and the filtrate was evaporated under vacuum. The residue was purified on flash silica gel column chromatography (CH2Cl2: MeOH=20:1) to give compound 207 (3 mg, 62%). 1H NMR (CD3OD, 400 MHz) δ 8.65-8.58 (m, 1H),

Workup

  1. additionAfter addition
  2. customwas brought to room temperature
  3. filtrationThe reaction mixture was filtered on a Celite bed
  4. customthe filtrate was evaporated under vacuum
  5. customThe residue was purified on flash silica gel column chromatography (CH2Cl2: MeOH=20:1)

Sources & evidence

ORD record
ord-cde9e582aeac4615879c827be46a7fae
Source dataset
uspto-grants-2013_08
Patent number
US08518957B2

Reaction notes

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